Water → Methyl 4-bromo-2-nitrobenzoate

HRID 2353869Notes

Reaction equation

HRID 2353869 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([N+:16]([O-:18])=[O:17])[CH:8]=1.O.[C:20](=O)([O-])[O-].[Na+].[Na+]>CO>[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH3:20])=[O:12])=[C:9]([N+:16]([O-:18])=[O:17])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 37744674-Bromo-2-nitrobenzoic acid

Product 1

HCID 18350461Methyl 4-bromo-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add concentrated sulfuric acid (7 mL) to a solution of commercially available 4-bromo-2-nitrobenzoic acid (25.0 g, 102 mmol) in methanol (150 mL), and heat at reflux for 16 hours. Cool the reaction to room temperature and pour into water (500 mL) and adjust the pH of the suspension to 9 with solid sodium carbonate. Extract the solution with ethyl acetate (2×250 mL), then combine the organic extracts and wash with brine (100 mL), dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford the title compound as a pale amber oil, which crystallizes upon standing (20.5 g, 78%)

Workup

  1. temperatureheat
  2. temperatureat reflux for 16 hours
  3. temperatureCool
  4. customthe reaction to room temperature
  5. extractionExtract the solution with ethyl acetate (2×250 mL)
  6. washwash with brine (100 mL)
  7. dry with materialdry over sodium sulfate
  8. filtrationfilter
  9. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-5ec9d999f4ce42f2b1120c32f369e08b
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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